Dimethylformamide → HCID 58293835, compound

To a solution of Compound 1036 (2.25 g, 7.885 mmol) in DCM (35 mL) was added 0.1 mL of DMF followed by addition of oxalyl chloride (1.502 g, 1.032 mL, 11.83 mmol). The reaction mixture was stirred at RT for 1 hour and the volatiles were removed in vacuo. The residue was taken up in benzene and the volatiles were again removed in vacuo (2×), followed by drying under vacuum. The residue was taken up in dry DCM (35 mL) and AlCl3 (3.679 g, 27.59 mmol) was added at RT. The mixture was stirred at RT for 1.5 hours and the reaction quenched with ethanol. The resulting solution was poured into ice water and extracted with DCM (2×). The combined organic layers were dried over Na2SO4, concentrated under vacuum, and the residue purified by silica gel chromatography, using a 5%-20% ethyl acetate/hexanes gradient as eluant, to produce ethyl 7-ethyl-4-oxo-7,8-dihydro-4H-thieno[2,3-d]azepine-6(5H)-carboxylate (Compound 1037, 671 mg).

1. customthe volatiles were removed in vacuo
2. customthe volatiles were again removed in vacuo (2×)
3. customby drying under vacuum
4. stirringThe mixture was stirred at RT for 1.5 hours
5. customthe reaction quenched with ethanol
6. additionThe resulting solution was poured into ice water
7. extractionextracted with DCM (2×)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. concentrationconcentrated under vacuum
10. customthe residue purified by silica gel chromatography

ORD record

ord-aae349ccdeca46cab16358327161d829

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481524B2